How To Have Anal Sex Guide

There are so many things that I didn’t know about anal sex before losing my anal virginity, which I sort of just discovered and learned with experience. These days, with the internet, it’s possible to be prepared and confident your very first time! Lucky you!

As much as porn would like you believe that you can just lube up and shove it in, it ain’t so. I mean, sure, in the realm of possibilities, that COULD happen… but if that’s your first time it’s going to be traumatic. Like, really traumatic. So read this ‘how to have anal sex guide’ and you’ll be good to go when the big moment happens!

I have read all these how-to guides and they all say ‘it shouldn’t hurt’, like you’re doing something wrong if it does. This isn’t really true. Everybody’s body is different, and just because somebody is loosey goosey, doesn’t mean that everybody is. The first time, there will probably be a lot of discomfort, and possibly some pain. Hell, even after years of experience, once in a while when your partner tries to enter too quickly it can hurt. But with proper preparation, a lot of patience, COMMUNICATION, and trust/alcohol, this will go away and you’ll be in the game! Anal sex takes some finesse to be successful and enjoyable. So don’t feel like you’re doing something wrong if it hurts… just take it out for a few seconds and breathe deeply.

The points below are what I have personally found to be the most help when acting as the receiving partner in penetrative sex (aka, the bottom). I hope my experience can be of some assistance to you as well!


How to have anal sex: Guide



Douche – As the name of this website will imply, I always like to start off with a good anal douching. No, you don’t HAVE to douche. However, I like to feel completely confident in the situation down there before having somebody’s fingers, mouth, penis or toys go at me like *insert some crude simile here*.

To learn more about douching, check out the MAD Anal Douching Guide, which will fully inform you about the process and catch you up to speed.

After douching I usually take a shower (or finish showering, if you are using a shower attachment douche) and wash off. Take this opportunity to apply some body wash or mild soap to your anus. Make sure you rinse thoroughly and don’t leave soap on or in your sphincter. This shower also relaxes you and gives you a chance to…


Play with yourself – Get to know your anus. I know that sounds cheesy, but really, it’s a must. Especially if it is your first time having anal sex, it’s very important to do some poking and prodding with your fingers and accustom yourself to the sensation of it all.

(This can also be done on your own, when not anticipating anal penetration. Getting to know what you like will help you feel more confident in guiding your partner, or exploring new things with them when it does come to two person play!)

After cleaning yourself off, apply some lube to your finger (not soap). Gently rub around your sphincter and get comfortable with having action going on down there. Push and prod and loosen yourself up. If it’s your first time it will definitely feel a little odd to have something pushing from the opposite side, but you’ll learn to relax and enjoy it.

Make an effort to relax your body. The easiest way to do this is to lay down. Either in the tub, on your bed, the kitchen floor, wherever is comfortable for you.

When you are ready, slip that liberally lubed finger inside your anus. This will probably feel a little odd and slightly uncomfortable. Just try and relax. There is NO RUSH. Take your finger out as necessary, add more lube as necessary and slowly feel your way.

Find out what you enjoy. Try different lubes, different angles, different speeds. Every slight change will lead to new sensations to work with and discover! Another great option is to use some anal toys, like butt plugs or dildos, to get used to feeling of entry down there.


Towels – Before you jump into bed, bring a towel. Anal sex can require a LOT of lube and having something to wipe your hands on/lay on you will be a lifesaver (especially if you enjoy using silicone lube, which is ultra-slick, but ends up staining sheets). An extra towel will never go unused in a hot, steamy anal session!



Foreplay – Remember the ‘get to know yourself’ segment we touched on earlier? Do this with your partner!

*From this point on, communication is key! Don’t be afraid to be vocal about what’s going on. Let your partner know what makes you feel good, and what you aren’t super fond of. It will make the whole experience more likely to be a success and will open up door to future discovery for the next round!*

It’s important to get your partner to warm you up before diving in, dick first. A lot of ‘tops’ (partners who penetrate) enjoy rimming their partners (think analingus). This can be an acquired feeling, as with most anal sensations. I certainly didn’t enjoy it at first, but now it’s almost necessary! It really helps let your body know what’s about it happen to it, and your muscles will relax and be more receptive to the experience.

Playing with fingers and lube is always a staple too, and can be extremely enjoyable while kissing your partner. You’d be surprised at how natural it feels to move your body with your partners while getting fingered. Again, try to relax as much as possible. It can be a shock at first!

Don’t forget to communicate with your partner what you’re enjoying and what you aren’t.  Hint: Moaning in different tones is often enough of an indicator, so is saying ‘yes’ or ‘takeitouttakeitoutTAKEITOUT!’.


Condoms – I’ll do my part for the anal community here and put in a plug for safe sex. I’m sure many of the readers on this site are in monogamous relationships and have made up their minds about the level of trust they share and how they will have sex/are having sex with each other. However, I feel it to be my duty to say “protect yourselves!” you are your number one defense!

While babies aren’t a consequence of anal intercourse, there are actually a few good reasons to use condoms while practicing anal sex:

1 – You can avoid any direct penis/faeces contact with any accidental particles which might be lingering down there by wearing a condom. However, by following this guide, that shouldn’t be an issue!

2 – The rectal lining is ultra-thin and susceptible to tearing, which means that anal sex is a ‘high risk’ activity.  This means that any infected body fluid exchanged during anal intercourse is more likely to absorbed by the bottom… Yes. Bottom’s unfortunately are more likely to pick up STIs. That’s not to say that tops cannot pick up new friends from the transaction, it’s just as important for them to wear protection also!

3 – Just be responsible


Lube – Oh my god, I cannot say enough about lube!! In fact, you need to read up about the different kinds of lube and why they matter, if you haven’t already!



Ok, while you have probably used lube while douching, playing with your ass and foreplay, if you haven’t, now is the time to apply it. Liberally. Apply it to your partner’s penis (or toy), as well as to your own anus.

Once you actually start penetration, the absorbent lining in your rectum will probably claim a lot of it, so apply more!

The rule of thumb is: Just when you think you’ve applied enough lube, apply twice that!


Trust – Communicate with your partner everything. I know I’ve mentioned this before, but it’s really so important. Always let your partner know how you’re feeling and what’s working/what’s not. Especially when penetration starts.


Penetration – It doesn’t really matter what position you’re in, the first time you have a penis inside you is going to feel like nothing else, and not necessarily in a good way.

This is usually the point where you need to remind the top that this isn’t about them, and that you’ll be ready when you are ready. Just like when you are playing with fingers, GO SLOW.

So you and your partner are lubed up, and they start pushing in. It feels alright for a split second and then all of a sudden ABORT – ABORT – ABORT! That’s normal, and something that I never read on other guides. Going slow isn’t enough. You need to let your sphincter know that you are purposefully putting a penis through it and that you didn’t just slip and land on a toilet plunger handle!

I always find the ‘give an inch, take an inch’ method to be the best. Seriously, barely push in, and then remove it all. Do this several times, sort of like teasing the anus. This will let your body know that it’s all right and you are in control of the situation. You should find after a couple of minutes, that your ass will be a lot more receptive to an invasive object. This is when you can slowly continue inserting the penis inside your body.

When you are being entered, try to think about keeping the pelvic muscles relaxed and breathe deeply. It can actually be a huge help to push out against your partner (yes, like you are trying to push out a shit), this makes it easier to for the penis to pass through the sphincter.

Trust me, it will feel awkward and uncomfortable, and you might feel some pain. Pull out, relax and try again. At some point, you’ll realize ‘Hey, I’m good to go!’. Your body will understand what’s happening and relax to a point where it feels totally pleasurable (for both parties!).

Take your time, listen to your body, and communicate with your partner!



I find that there are three positions which are good, for different reasons, while first being entered by your partner.


1 – Spooning

Laying on your sides, little spoon being the bottom obviously, the body is completely relaxed and it’s easier to keep control over your tense pelvic muscles. This allows the penetratee to push back against the partner at their own pace, keeping the control in their hands.

It’s also very easy to flip into a face-down-in-the-pillow position once the bottom is comfortable, tons of fun!


2 – Missionary Position

The bottom on their back with their legs up, either resting on the top’s shoulders, or held close to the body.

This position is much more comfortable for the bottom if they are reasonably flexible and can pull their legs in close. This lets the body relax and makes it easier to receive.

Remember, because this gives the power to the top to decide pace, communication is extremely important. Let each other know what’s going on… More so, bottom, let your top know if you’re doing alright!


3 – Bottom on top

This position allows the bottom to be in control of how much and how fast.

The top lays on his back, giving the bottom access to his penis. The receiver can then lower themselves down onto the top, and when they are ready to take in more, they can.


From then on it’s just a listen-to-your-body game. Once you relax it can be a LOT of fun!

Remember. LUBE UP! After a few thrusts you’ll need to reapply (unless you are using silicone lube which stays slick forever… even then, apply some more). It will be an unbelievable help and can mean the difference between a good experience, and never trying it again!

I hope this basic anal sex guide has been of some sort of help to you! I know there are a lot of things to think about, but it really is a blast and it’s totally worth the extra effort.

Where to from here? Check out the My Anal Douche homepage, or do a bit of reading on the best anal lubes!

Adios, anal adventurers!

– Jason